US5001844A - Method of drying carrageenans - Google Patents

Method of drying carrageenans Download PDF

Info

Publication number
US5001844A
US5001844A US07/529,567 US52956790A US5001844A US 5001844 A US5001844 A US 5001844A US 52956790 A US52956790 A US 52956790A US 5001844 A US5001844 A US 5001844A
Authority
US
United States
Prior art keywords
carrageenans
drying
fibers
dried
liquid media
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Fee Related
Application number
US07/529,567
Inventor
Jean-Pierre Lhonneur
Jacky Lefrancois
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Elf Sanofi SA
Original Assignee
Sanofi SA
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Sanofi SA filed Critical Sanofi SA
Assigned to SANOFI, reassignment SANOFI, ASSIGNMENT OF ASSIGNORS INTEREST. Assignors: LEFRANCOIS, JACKY, LHONNEUR, JEAN-PIERRE
Application granted granted Critical
Publication of US5001844A publication Critical patent/US5001844A/en
Assigned to ELF SANOFI reassignment ELF SANOFI CHANGE OF NAME (SEE DOCUMENT FOR DETAILS). Assignors: SANOFI
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08BPOLYSACCHARIDES; DERIVATIVES THEREOF
    • C08B37/00Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
    • C08B37/0006Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid
    • C08B37/0036Galactans; Derivatives thereof
    • C08B37/0042Carragenan or carragen, i.e. D-galactose and 3,6-anhydro-D-galactose, both partially sulfated, e.g. from red algae Chondrus crispus or Gigantia stellata; kappa-Carragenan; iota-Carragenan; lambda-Carragenan; Derivatives thereof
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23LFOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L29/00Foods or foodstuffs containing additives; Preparation or treatment thereof
    • A23L29/20Foods or foodstuffs containing additives; Preparation or treatment thereof containing gelling or thickening agents
    • A23L29/206Foods or foodstuffs containing additives; Preparation or treatment thereof containing gelling or thickening agents of vegetable origin
    • A23L29/256Foods or foodstuffs containing additives; Preparation or treatment thereof containing gelling or thickening agents of vegetable origin from seaweeds, e.g. alginates, agar or carrageenan

Definitions

  • the present invention relates to a method of drying carrageenans, these being sulfated polysaccharides which are very widely used in the food industry for thickening, gelling or stabilizing suspensions, more particularly in milk-based media, and to the resulting carrageenans of improved dispersibility.
  • Carrageenans are extracted from red algae and more particularly from Chrondrus crispus, Euchema cottonii, Euchema spinosum or Irideae species; depending on their origin, different types of carrageenan, called lambda, iota or kappa carrageenans, are obtained which differ slightly in structure and properties.
  • these products are obtained by macerating the group algae in hot water which has been rendered alkaline; after a few hours, the insoluble materials are separated off by hot filtration and the carrageenan is coagulated by the addition of an alcoholic solvent to the filtrate, generally by the addition of isopropanol.
  • the fibers formed are isolated by filtration, drained and then rewashed with isopropanol before being drained again.
  • the white fibrous mass obtained contains about 55% of polysaccharide, 15% of isopropanol and 30% of water. It is then dried under a paratial vacuum, at a temperature of between about 40° C. and 60° C., generally until the solids content is 10%.
  • the fibers are then ground to give a low-density powder, which is rather difficult to handle and to bag. Moreover--and this is a major disadvantage--the powder is difficult to disperse in liquids, including milk, and if the dispersion is not agitated vigorously and the powder is not added slowly, lumps and aggregates form in the preparation.
  • the dispersibility of the polysaccharide is improved by compacting the moist fibers to a solids content of 20% in compacting rollers under a pressure of more than 10 8 Pa; after grinding, a powder is isolated which still consists of broken filaments but whose density is greater than that of the powder obtained direct, for example 0.7 to 0.8 instead of 0.3 to 0.4, and, in particular, whose dispersibility in water or milk is satisfactory; nevertheless, this method has a number of disadvantages, including the cost of investment in equipment and a certain operating difficulty, especially because it is complicated to feed the compacter continuously with the fibers.
  • Another way of improving the dispersibility which may be considered is to mix with the powder a small proportion of an edible surfactant such as lecithin or sorbitan esters.
  • an edible surfactant such as lecithin or sorbitan esters.
  • the use of these products is not authorized in all countries and, in particular, they are not transparent in aqueous solution.
  • carrageenans as a mixture with bulking agents, for example sugars or salts, but this is unsuitable for some applications.
  • drying the moist fibers under particular conditions produces a powder which is fairly dense and readily dispersible in aqueous or milky media and which also has substantially the same physicochenmical properties as the powder obtained by conventional drying.
  • the method according to the invention consists in drying the water-impregnated fibers in a microwave chamber at ordinary pressure instead of drying them in a dryer under vacuum at a temperature of between 40° C. and 60° C. and under a pressure of between about 10 5 and 10 6 Pa.
  • the water-impregnated fibers will contain from 20% to 100% of their weight of water.
  • These fibers can be those isolated at the end of the extraction process after washing and draining; apart from water, there is then a certain amount of isopropanol and, especially because of the risks of ignition and the toxicity of the alcohol, it is preferred to predry the mass in a conventional oven, under vacuum if necessary, until the isopropanol content is reduced to 5% or less.
  • This method can also be applied to the fibers dried in conventional manner, after they have been mixed with a small amount of water in a malaxator; the proportions of water of be used can vary within wide limits; in general, it suffices to make the fibers into a paste again with the same weight of water.
  • Drying can be carried out using any microwave oven such as those currently marketed for drying industrial products by the company FAMO--Villefranche S/Saone (FR), of the AIMT AM series, or by the companies APV Magnetronics (GB) or IMI Epone (FR).
  • FR the company FAMO--Villefranche S/Saone
  • GB APV Magnetronics
  • IMI Epone FR
  • these apparatuses have an emission frequency of 915 or 2450 MHz, but this frequency is not critical and it is possible to use emitters between 100 and 10,000 MHz when their use is authorized in the country in which the operation is carried out.
  • the operation is preferably carried out with devices which permit continuous drying, the carrageenans being introduced into the irradiated zone by a conveyor belt made of a material inert to microwaves.
  • the appearance of the fibers is not modified during this drying operation, in contrast to what is observed with other macromolecules and especially with proteins such as egg white, whose macroscopic network is expanded when they are subjected to microwaves in the presence of water.
  • the density of the powder obtained after grinding of the fibers dried in this way is greater than that of the powder obtained after conventional drying.
  • the lambda and iota carrageenans are generally dried, by the conventional method, until the solids content is 90 to 92%; they can be ground and they give a fluid powder; with microwave drying, however, it suffices to have a solids content of 83 to 85%, which will be sufficiently dense to give a non-flaky powder with a solids content of 90-95% after grinding.
  • the dispersibility of the powders in aqueous or milky media is improved: appreciably fewer lumps are formed with gentle agitation or without raising the temperature.
  • a further advantage of the method according to the invention is that is improves the bacteriological quality of the powder obtained: the number of germs per gram is less than that in the case of conventional drying.
  • the powder dried in this way has the same rheological properties as a powder dried under the conventional conditions and its taste is not modified; it can also be used in all the conventional applications of carrageenans, such as cocoa-flavored milk, ice creams, baked custards and analogous products.
  • a microwave oven emitting at 2450 MHz is used.
  • the carrageenan which is a compressed extract of Euchema cottonii containing 35% of water and 15% of isopropanol by weight, is predried to 30% of water and 15% of isopropanol and is then introduced into the oven on a conveyor belt on which it has been deposited to a uniform thickness of between 5 and 10 cm; the speed of the belt depends on the length of the oven, the amount of water in the product when it enters and the solids content fixed for the product when it leaves.
  • the mean residence time is 5 to 15 minutes for a product containing about 30% of water when it enters an oven equipped with forty-eight 800 watt generators; the resulting carrageenan fibers, which have a solids content of 93-94%, are ground in a hammer mill, in the same way as the fibers obtained from a vacuum dryer, and are then sieved.
  • the powder obtained is homogeneous, fluid and does not agglomerate, in contrast to that resulting from conventional drying.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Polymers & Plastics (AREA)
  • Biochemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Nutrition Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Dispersion Chemistry (AREA)
  • Materials Engineering (AREA)
  • Food Science & Technology (AREA)
  • Medicinal Chemistry (AREA)
  • Organic Chemistry (AREA)
  • Edible Seaweed (AREA)
  • Polysaccharides And Polysaccharide Derivatives (AREA)
  • Confectionery (AREA)
  • Jellies, Jams, And Syrups (AREA)
  • Artificial Filaments (AREA)

Abstract

The invention relates to a method of drying carrageenans extracted from red algae by alkaline treatment in an aqueous medium. This method consists in subjecting the moist fibers to the action of microwaves at 100 to 10,000 MHz in such a way that the temperature of the mass does not exceed 100° C. Application: preparation of carrageenans.

Description

The present invention relates to a method of drying carrageenans, these being sulfated polysaccharides which are very widely used in the food industry for thickening, gelling or stabilizing suspensions, more particularly in milk-based media, and to the resulting carrageenans of improved dispersibility.
Carrageenans are extracted from red algae and more particularly from Chrondrus crispus, Euchema cottonii, Euchema spinosum or Irideae species; depending on their origin, different types of carrageenan, called lambda, iota or kappa carrageenans, are obtained which differ slightly in structure and properties.
Industrially, these products are obtained by macerating the group algae in hot water which has been rendered alkaline; after a few hours, the insoluble materials are separated off by hot filtration and the carrageenan is coagulated by the addition of an alcoholic solvent to the filtrate, generally by the addition of isopropanol. The fibers formed are isolated by filtration, drained and then rewashed with isopropanol before being drained again. The white fibrous mass obtained contains about 55% of polysaccharide, 15% of isopropanol and 30% of water. It is then dried under a paratial vacuum, at a temperature of between about 40° C. and 60° C., generally until the solids content is 10%. The fibers are then ground to give a low-density powder, which is rather difficult to handle and to bag. Moreover--and this is a major disadvantage--the powder is difficult to disperse in liquids, including milk, and if the dispersion is not agitated vigorously and the powder is not added slowly, lumps and aggregates form in the preparation.
The dispersibility of the polysaccharide is improved by compacting the moist fibers to a solids content of 20% in compacting rollers under a pressure of more than 108 Pa; after grinding, a powder is isolated which still consists of broken filaments but whose density is greater than that of the powder obtained direct, for example 0.7 to 0.8 instead of 0.3 to 0.4, and, in particular, whose dispersibility in water or milk is satisfactory; nevertheless, this method has a number of disadvantages, including the cost of investment in equipment and a certain operating difficulty, especially because it is complicated to feed the compacter continuously with the fibers.
Another way of improving the dispersibility which may be considered is to mix with the powder a small proportion of an edible surfactant such as lecithin or sorbitan esters. However, the use of these products is not authorized in all countries and, in particular, they are not transparent in aqueous solution.
It has also been recommended to use carrageenans as a mixture with bulking agents, for example sugars or salts, but this is unsuitable for some applications.
It has now been found that drying the moist fibers under particular conditions produces a powder which is fairly dense and readily dispersible in aqueous or milky media and which also has substantially the same physicochenmical properties as the powder obtained by conventional drying.
The method according to the invention consists in drying the water-impregnated fibers in a microwave chamber at ordinary pressure instead of drying them in a dryer under vacuum at a temperature of between 40° C. and 60° C. and under a pressure of between about 105 and 106 Pa.
Before being subjected to the action of microwaves, the water-impregnated fibers will contain from 20% to 100% of their weight of water.
These fibers can be those isolated at the end of the extraction process after washing and draining; apart from water, there is then a certain amount of isopropanol and, especially because of the risks of ignition and the toxicity of the alcohol, it is preferred to predry the mass in a conventional oven, under vacuum if necessary, until the isopropanol content is reduced to 5% or less.
This method can also be applied to the fibers dried in conventional manner, after they have been mixed with a small amount of water in a malaxator; the proportions of water of be used can vary within wide limits; in general, it suffices to make the fibers into a paste again with the same weight of water.
Drying can be carried out using any microwave oven such as those currently marketed for drying industrial products by the company FAMO--Villefranche S/Saone (FR), of the AIMT AM series, or by the companies APV Magnetronics (GB) or IMI Epone (FR). Generally, in France, these apparatuses have an emission frequency of 915 or 2450 MHz, but this frequency is not critical and it is possible to use emitters between 100 and 10,000 MHz when their use is authorized in the country in which the operation is carried out.
It is known that, on average, 1 kg of water is evaporated per kW supplied per hour, and the treatment time depends essentially on the quantity of energy received per unit volume, the quantity of moisture initially present in the mass and the thickness of the latter, but it is important that the temperature inside the mass of carrageenan should not exceed 100° C. or preferably 95° C., so as to avoid any decomposition of the polysaccharide.
The operation is preferably carried out with devices which permit continuous drying, the carrageenans being introduced into the irradiated zone by a conveyor belt made of a material inert to microwaves.
The appearance of the fibers is not modified during this drying operation, in contrast to what is observed with other macromolecules and especially with proteins such as egg white, whose macroscopic network is expanded when they are subjected to microwaves in the presence of water. On the contrary, the density of the powder obtained after grinding of the fibers dried in this way is greater than that of the powder obtained after conventional drying.
The kappa carrageenans and their gelling mixtures with the lambda and iota carrageenans, dried by the conventional method until the solids content is 95%, are flaky and the fibers, which are difficult to grind, always give a cottony powder of density 0.3-0.4; by contrast, with microwave drying, the fibers with a solids content of 93-95% can be ground and they give a powder with a greater density of about 0.5, which is fluid and non-cottony.
The lambda and iota carrageenans are generally dried, by the conventional method, until the solids content is 90 to 92%; they can be ground and they give a fluid powder; with microwave drying, however, it suffices to have a solids content of 83 to 85%, which will be sufficiently dense to give a non-flaky powder with a solids content of 90-95% after grinding.
Moreover, the dispersibility of the powders in aqueous or milky media is improved: appreciably fewer lumps are formed with gentle agitation or without raising the temperature.
A further advantage of the method according to the invention is that is improves the bacteriological quality of the powder obtained: the number of germs per gram is less than that in the case of conventional drying.
The powder dried in this way has the same rheological properties as a powder dried under the conventional conditions and its taste is not modified; it can also be used in all the conventional applications of carrageenans, such as cocoa-flavored milk, ice creams, baked custards and analogous products.
An Example of the method according to the invention is described below.
EXAMPLE:
A microwave oven emitting at 2450 MHz is used. The carrageenan, which is a compressed extract of Euchema cottonii containing 35% of water and 15% of isopropanol by weight, is predried to 30% of water and 15% of isopropanol and is then introduced into the oven on a conveyor belt on which it has been deposited to a uniform thickness of between 5 and 10 cm; the speed of the belt depends on the length of the oven, the amount of water in the product when it enters and the solids content fixed for the product when it leaves. In general, with a belt speed of 0.1 to 5 m/min, the mean residence time is 5 to 15 minutes for a product containing about 30% of water when it enters an oven equipped with forty-eight 800 watt generators; the resulting carrageenan fibers, which have a solids content of 93-94%, are ground in a hammer mill, in the same way as the fibers obtained from a vacuum dryer, and are then sieved. The powder obtained is homogeneous, fluid and does not agglomerate, in contrast to that resulting from conventional drying.

Claims (8)

What is claimed is:
1. A method of drying carrageenans extracted from red algae by alkaline treatment in an aqueous medium, wherein the moist fibers are subjected to the action of microwaves at 100 to 10,000 MHz in such a way that the temperature of the mass does not exceed 100° C.
2. A method according to claim 1, wherein the fibers are predried to remove the isopropanol until the isopropanol content is reduced to 5% or less.
3. A method according to claim 1, wherein the frequency of the microwaves is 2450 MHz.
4. A method according to claim 1, which is carried out continuously, the carrageenans being introduced into the microwave oven on a conveyor belt.
5. Kappa carrageenans having an improved dispersibility in liquid media, which are dried by the method according to claim 1.
6. Kappa carrageenans as a mixture with iota and lambda carrageenans, having an improved dispersibility in liquid media, wherein the extract of red algae is dried by the method according to claim 1.
7. Kappa carrageenans having an improved dispersibility in liquid media, which are dried by the method according to claim 2.
8. Kappa carrageenans as a mixture with iota and lambda carrageenans, having an improved dispersibility in liquid media, wherein the extract of red algae is dried by the method according to claim 2.
US07/529,567 1989-06-01 1990-05-29 Method of drying carrageenans Expired - Fee Related US5001844A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR8907256 1989-06-01
FR8907256A FR2647884B1 (en) 1989-06-01 1989-06-01 CARRAGHENANES DRYING PROCESS

Publications (1)

Publication Number Publication Date
US5001844A true US5001844A (en) 1991-03-26

Family

ID=9382268

Family Applications (1)

Application Number Title Priority Date Filing Date
US07/529,567 Expired - Fee Related US5001844A (en) 1989-06-01 1990-05-29 Method of drying carrageenans

Country Status (8)

Country Link
US (1) US5001844A (en)
EP (1) EP0401116B1 (en)
CA (1) CA2018019A1 (en)
DE (1) DE69006264T2 (en)
DK (1) DK0401116T3 (en)
ES (1) ES2050974T3 (en)
FR (1) FR2647884B1 (en)
IE (1) IE64120B1 (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5484606A (en) * 1994-01-24 1996-01-16 The Procter & Gamble Company Process for reducing the precipitation of difficulty soluble pharmaceutical actives
US20130150810A1 (en) * 2002-04-30 2013-06-13 The Population Council, Inc. Intravaginal ring for the delivery of unique combinations of antimicrobial compositions

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2061728A (en) * 1979-10-24 1981-05-20 Colgate Palmolive Co Stabilization of carrageenan-containing cosmetic compositions
US4276320A (en) * 1980-01-25 1981-06-30 Fmc Corporation Compositions and method for preparing dessert gels
US4720924A (en) * 1986-11-03 1988-01-26 R & J Engineering Corporation Microwave drying of pharmaceutical gelatin capsules
US4896434A (en) * 1988-11-10 1990-01-30 Joseph Fanelli Apparatus and method for drying gel
US4915506A (en) * 1987-09-10 1990-04-10 Hosokawa Micron Europe B.V. Apparatus for drying material which is mixed with a solvent

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5832576B2 (en) * 1976-10-28 1983-07-14 協和醗酵工業株式会社 Method for modifying gelatin
US4096327A (en) * 1977-01-05 1978-06-20 Fmc Corporation Modified kappa-carrageenan
JPS54117045A (en) * 1978-03-03 1979-09-11 Yoichi Hirata Food coagulating agent
JPS5973043A (en) * 1982-10-19 1984-04-25 House Food Ind Co Ltd Method for modifying quality of hardly soluble gelling agent
JPH0662400B2 (en) * 1985-11-11 1994-08-17 佐藤製薬株式会社 Sugar-coated tablets
JPS62138171A (en) * 1985-12-11 1987-06-20 Hideya Onodera Production of algae noodle useful as health food

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2061728A (en) * 1979-10-24 1981-05-20 Colgate Palmolive Co Stabilization of carrageenan-containing cosmetic compositions
US4276320A (en) * 1980-01-25 1981-06-30 Fmc Corporation Compositions and method for preparing dessert gels
US4720924A (en) * 1986-11-03 1988-01-26 R & J Engineering Corporation Microwave drying of pharmaceutical gelatin capsules
US4915506A (en) * 1987-09-10 1990-04-10 Hosokawa Micron Europe B.V. Apparatus for drying material which is mixed with a solvent
US4896434A (en) * 1988-11-10 1990-01-30 Joseph Fanelli Apparatus and method for drying gel

Non-Patent Citations (8)

* Cited by examiner, † Cited by third party
Title
Derwent Abstract C85 113296, House Shokuhin Kogy. *
Derwent Abstract C85-113296, House Shokuhin Kogy.
Derwent Abstract C89 042441, Taguchi. *
Derwent Abstract C89-042441, Taguchi.
Derwent File Supplier, No. AN 79 764 55B, 1979, Hirata. *
Derwent File Supplier, No. AN 87 210585, 1987, Onodera. *
Derwent File Supplier, No. AN-79-764 55B, 1979, Hirata.
Derwent File Supplier, No. AN-87-210585, 1987, Onodera.

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5484606A (en) * 1994-01-24 1996-01-16 The Procter & Gamble Company Process for reducing the precipitation of difficulty soluble pharmaceutical actives
US20130150810A1 (en) * 2002-04-30 2013-06-13 The Population Council, Inc. Intravaginal ring for the delivery of unique combinations of antimicrobial compositions

Also Published As

Publication number Publication date
FR2647884B1 (en) 1994-12-02
FR2647884A1 (en) 1990-12-07
EP0401116B1 (en) 1994-01-26
ES2050974T3 (en) 1994-06-01
IE901961L (en) 1990-12-01
IE64120B1 (en) 1995-07-12
DK0401116T3 (en) 1994-05-24
EP0401116A1 (en) 1990-12-05
CA2018019A1 (en) 1990-12-01
DE69006264T2 (en) 1994-08-04
DE69006264D1 (en) 1994-03-10

Similar Documents

Publication Publication Date Title
Yarnpakdee et al. Physico-chemical and gel properties of agar from Gracilaria tenuistipitata from the lake of Songkhla, Thailand
EP1641832B1 (en) Method for preparing fibre-containing pectin and products and uses hereof
CN114025619A (en) Natural composite material derived from seaweed and method for producing the same
WO2019217489A1 (en) Seaweed meal and method of making the same
US3120233A (en) Method for manufacturing recon-stituted tobacco products
CN109054053A (en) A kind of processing technology of high-gel strength agar
US5001844A (en) Method of drying carrageenans
US4357467A (en) Depolymerized cellulosic material with low crystallinity obtained from cellulosic fibers and process for its manufacture
AU741977B2 (en) Methods of obtaining selected pectin fractions, such fractions and their use
US4286087A (en) Chitin powder and process for making it
JP3075493B2 (en) Method for producing powdered chitosan
RU2140927C1 (en) Method of preparing pectin from sunflower calathides
EP4223128A1 (en) Use of an activatable, deesterified, pectin-converted fruit fiber for making sausages without added phosphates or meat substitutes
US2620334A (en) Process of extraction from irish moss
CA2046187A1 (en) Process for the production of kappa carrageenans
US3476741A (en) Method for treating polysaccharides in the presence of an oxygen accepting agent
RU2175844C1 (en) Method of preparing food fiber from beet pulp
JPH046384B2 (en)
US4286062A (en) Process for producing an enzyme preparation to tenderize meat products
KR0139650B1 (en) Process for preparing micro crystalline chitin
RU2035478C1 (en) Method of preparing black dye for foodstuffs
JPH0258542A (en) Dehydration and pulverization of polymer substance
US2231283A (en) Manufacture of irish moss
RU2086151C1 (en) Method of preparing feed additive from vegetable raw material
RU2080081C1 (en) Method of preparing the dry pectin extract from plant raw and a method of preparing pectin from plant raw

Legal Events

Date Code Title Description
AS Assignment

Owner name: SANOFI,, FRANCE

Free format text: ASSIGNMENT OF ASSIGNORS INTEREST.;ASSIGNORS:LHONNEUR, JEAN-PIERRE;LEFRANCOIS, JACKY;REEL/FRAME:005376/0333

Effective date: 19900621

AS Assignment

Owner name: ELF SANOFI, FRANCE

Free format text: CHANGE OF NAME;ASSIGNOR:SANOFI;REEL/FRAME:006763/0399

Effective date: 19931112

FEPP Fee payment procedure

Free format text: PAYOR NUMBER ASSIGNED (ORIGINAL EVENT CODE: ASPN); ENTITY STATUS OF PATENT OWNER: LARGE ENTITY

FEPP Fee payment procedure

Free format text: PAYOR NUMBER ASSIGNED (ORIGINAL EVENT CODE: ASPN); ENTITY STATUS OF PATENT OWNER: LARGE ENTITY

Free format text: PAYER NUMBER DE-ASSIGNED (ORIGINAL EVENT CODE: RMPN); ENTITY STATUS OF PATENT OWNER: LARGE ENTITY

FPAY Fee payment

Year of fee payment: 4

FEPP Fee payment procedure

Free format text: PAYER NUMBER DE-ASSIGNED (ORIGINAL EVENT CODE: RMPN); ENTITY STATUS OF PATENT OWNER: LARGE ENTITY

FEPP Fee payment procedure

Free format text: PAYOR NUMBER ASSIGNED (ORIGINAL EVENT CODE: ASPN); ENTITY STATUS OF PATENT OWNER: LARGE ENTITY

REMI Maintenance fee reminder mailed
LAPS Lapse for failure to pay maintenance fees
FP Lapsed due to failure to pay maintenance fee

Effective date: 19990326

STCH Information on status: patent discontinuation

Free format text: PATENT EXPIRED DUE TO NONPAYMENT OF MAINTENANCE FEES UNDER 37 CFR 1.362